Oligomerization of humic phenolic monomers by oxidative coupling under biomimetic catalysis

Environmental Science and Technology

Volumn 40, Issue 22, 2006, Pages 6955-6962

  Šmejkalová, Daniela ^a   Piccolo, Alessandro ^a   Spiteller, Michael ^b  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; OLIGOMERS; OXIDATION; PORPHYRINS;

BIOMIMETIC CATALYSIS; OLIGOMERIZATION; PHENOLIC MONOMERS; TRIMERIZATION;

MONOMERS;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; CAFFEIC ACID; CARBOXYLIC ACID DERIVATIVE; CATECHOL; DIMER; IRON; METAL; MONOMER; NATURAL ORGANIC MATTER; OLIGOMER; PARA COUMARIC ACID; PHENOL DERIVATIVE; PORPHYRIN DERIVATIVE; WATER;

GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; MONOMERS; OLIGOMERS; OXIDATION; PORPHYRINS;

ORGANIC MATTER; OXIDATION; PHENOLIC COMPOUND; POLYMERIZATION;

AQUEOUS SOLUTION; ARTICLE; BIOMIMETICS; CATALYSIS; CHEMICAL STRUCTURE; DEGRADATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; OLIGOMERIZATION; OXIDATION; POLYMERIZATION;

BIOMIMETICS; CATALYSIS; DIMERIZATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMIC SUBSTANCES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENOLS; POLYMERS; PORPHYRINS;

EID: 33751102901     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es061127c     Document Type: Article

References (36)

1. Stevenson, F. J. Humus Chemistry: Genesis, Composition, and Reactions, 2nd ed.; John Wiley and Sons: New York, 1994.
2. Sánchez-Cortés, S.; Francioso, O.; García-Ramos, J. V.; Ciavatta, C.; Gessa, C. Catechol polymerization in the presence of silver surface. Colloids Surf., A 2001, 176, 177-184.
3. Martin, J. P.; Haider, K. Microbial activity in relation to soil humus formation. Soil Sci. 1971, 3, 54-63.
4. Sjobald, R. D.; Bollag, J.-M. Oxidative coupling of aromatic compounds by enzymes from soil microorganisms. In Soil Biochemistry; Paul, E. A., Ladd, J. N., Eds.; Marcel Dekker: New York, 1981.
5. Park, J.-W.; Dec, J.; Kim, J.-E.; Bollag, J.-M. Effect of humic constituents on the transformation of chlorinated phenols and anilines in the presence of oxidoreductive enzymes or birnessite. Environ. Sci. Technol. 1999, 33, 2028-2034.
6. Dec, J.; Bollag, J.-M. Phenoloxidase-mediated interactions of phenols and anilines with humic materials. J. Environ. Qual. 2000, 29, 665-676.
7. Dec, J.; Haider, K.; Bollag, J.-M. Decarboxylation and demethoxylation of naturally occurring phenols during coupling reactions and polymerization. Soil Sci. 2001, 166, 660-671.
8. Baciocchi, E.; Lanzalunga, O.; Lapi, A. Formation of quinones in the iron porphyrin catalyzed oxidation of benzene and alkylbenzenes by magnesium monoperoxyphtalate. Tetrahedron Lett. 1995, 36, 3547-3548.
9. Grabber, J. H.; Ralph, J.; Hatfield, R. D. Cross-linking of maize walls by ferulate dimerization and incorporation into lignin. J. Agric. Food Chem. 2000, 48, 6106-6113.
10. Dec, J.; Haider, K.; Bollag, J.-M. Release of substituents from phenolic compounds during oxidative coupling reaction. Chemosphere 2003, 52, 549-556.
11. Fournand, D.; Cathala, B.; Lapierre, C. Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde: capillary zone electrophoresis study of pH effect. Phytochemistry 2003, 62, 139-146.
12. Weber, W. J., Jr.; Huang, Q.; Pinto, A. R. Reduction of disinfection byproduct formation by molecular reconfiguration of the fulvic constituents of natural background organic matter. Environ. Sci. Technol. 2005, 39, 6446-6452.
13. Huang, Q.; Huang, Q.; Pinto, A. R.; Griebenow, K.; Schweitzer-Stenner, R.; Weber, W. J., Jr. Inactivation of horseradish peroxidase by phenoxyl radical attack. J. Am. Chem. Soc. 2005, 127, 1431-1437.
14. Gonsalves, A. M. dA. R.; Pereira, M. M. State of the art in the development of biomimetic oxidation catalysts. J. Mol. Catal. A 1996, 113, 209-221.
15. Piccolo, A.; Conte, P.; Tagliatesta, P. Increased conformational rigidity of humic substances by oxidative biomimetic catalysis. Biomacromolecules 2005, 6, 351-358.
16. Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. High-valent iron-porphyrin complexes related to peroxidase and cytochromeP-450. J. Am. Chem. Soc. 1981, 103, 2884-2886.
17. Sheldon, R. A. Oxidations catalysis by metalloporphyrins. In Metalloporphyrins in Catalytic Oxidations; Sheldon, R. A., Ed.; Dekker: New York, 1994.
18. Šmejkalová, D.; Piccolo, A. Rates of Oxidative Coupling of Humic Phenolic Monomers Catalyzed by a Biomimetic Iron-Porphyrin. Environ. Sci. Technol. 2006, 40, 1644-1649.
19. Cole, E. B. Electrospray ionization mass spectrometry. Fundamentals, instrumentation and applications: John Wiley and Sons: New York, 1997.
20. Guillén, M. D.; Ibargoitia, M. L. GC-MS analysis of lignin monomers, dimers and trimers in liquid smoke flavourings. J. Sci. Food Agric. 1999, 79, 1889-1903.
21. Benijts, T.; Dams, R.; Günter, W.; Lambert, W.; De, Leenheer, A. Analysis of estrogenic contaminants in river water using liquid chromatography coupled to ion trap based mass spectrometry. Rapid Commun. Mass Spectrom. 2002, 16, 1358-1364.
22. Quintana, J. B.; Carpinteiro, J.; Rodríguez, I.; Lorenzo, R. A.; Carro, A. M.; Cela, R. Determination of natural and synthetic estrogenes in water by gas chromatography with mass spectroscopic detection. J. Chromatogr., A 2004, 1024, 177-185.
23. Ichimura, K.; Yasuhiro, A.; Akiyama, H.; Kudo, K.; Hayashi, Y. Photoreactivity of polymers with regioisomeric cinnamate side chains and their ability to regulate liquid crystal alignment. Macromolecules 1997, 30, 903-911.
24. Grabber, J. H.; Ralph, J.; Hatfield, R. D. Cross-linking of maize walls by ferrulate dimerization and incorporation into lignin. J. Agric. Food Chem. 2000, 48, 6106-6113.
25. Ward, G.; Hadar, Y.; Bilkis, I.; Konstantinovsky, L.; Dosoretz, C. Initial steps of ferulic acid polymerization by lignin peroxidase. J. Biol. Chem. 2001, 276, 18734-18741.
26. Antolovich, M.; Bedgood, D. R., Jr.; Bishop, A. G.; Jardine, D.; Prenaler, P. D.; Robards, K. LC-MS investigation of oxidation products of phenolic antioxidants. J. Agric. Food Chem. 2004, 52, 962-971.
27. Silverstein, R. M.; Baasler, G. C.; Morril, T. C. Spectrometric identification of organic compounds, 4th ed.; John Wiley and Sons: New York, 1981.
28. Hapiot, P.; Neudeck, A.; Pinson, J.; Fulcrand, H.; Neta, P.; Rolando, C. Oxidation of caffeic acid and related hydroxycinnamic acids. J. Electroanal. Chem. 1997, 405, 169-176.
29. Sánchez-Cortés, S.; García-Ramos, J. V. Photoinduced coupling and adsorption of caffeic acid on silver surface studied by surface-enhanced Raman spectroscopy. Spectrochim. Acta, Part A 1999, 55, 2935-2941.
30. Tazaki, H.; Taguchi, D.; Hayashida, T.; Nabeta, K. Stable isotope-labeling studies on the oxidative coupling of caffeic acid via o-quinone. Biosci. Biotechnol. Biochem. 2001, 65, 2613-2621.
31. Pérez-Magariño, S.; Revilla, L.; Gonzáles- Sanjosé, M. L.; Beltrán, S. Various applications of liquid chromatography-mass spectrometry to the analysis of phenolic compounds. J. Chromatrogr., A 1999, 847, 75-81.
32. Sánchez-Rabaneda, F.; Jáuregui, O.; Casals, L; Andrés-Lacueva, C.; Izquierdo-Pulido, M.; Lamuela-Raventós, R. M. Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). J. Mass Spectrom. 2003, 38, 35-42.
33. Russell, W. R.; Burkitt, M. J.; Scobbie, L; Chesson, A. Radical formation and coupling of hydoxycinnamic acids containing 1,2-dihydroxysubstituents. Bioorg. Chem. 2003, 31, 206-215.
34. Ricaid, J.; Job, D. Reaction mechanisms of indole-3-acetate degradation by peroxidases. A stopped-flow and low-temperature spectroscopic study. Eur. J. Biochem. 1974, 44, 359-374.
35. Ma, Y.-A.; Guo, Z-W.; Sih, C. J. Enzymatic oxidative coupling of monohalogenated tyrosine derivatives. Tetrahedron Lett. 1998, 39, 9357-9360.
36. Traylor, P. S.; Dolphin, D.; Traylor, T. G. Sterically protected hemins with electronegative substituents: efficient catalysts for hydroxylation and epoxidation. J. Chem. Soc., Chem. Commun. 1984, 279-280.